diff --git a/src/dsl/walker/mod.rs b/src/dsl/walker/mod.rs
index c7d5c5a..2c6c662 100644
--- a/src/dsl/walker/mod.rs
+++ b/src/dsl/walker/mod.rs
@@ -1106,6 +1106,72 @@ fn compound_arity_diagnostics(
     diagnostics
 }
 
+/// `auto_column_overridden` WARNING (ADR-0033 §8.2, sub-phase 3i).
+///
+/// A SQL `INSERT` whose explicit column list names a `serial` or
+/// `shortid` column is providing a value for a column the playground
+/// auto-generates (`serial` via the engine rowid, `shortid` via the
+/// worker post-fill). That bypasses the auto-counter / generator and
+/// can collide with later auto-generated values — pedagogically worth
+/// a nudge, but advisory: the statement still runs (ADR-0027 §1).
+///
+/// The conflict-target column list of an `ON CONFLICT (…)` uses a
+/// distinct role (`conflict_target_column`), so it is not mistaken
+/// for an inserted column here.
+fn dml_auto_column_diagnostics(
+    path: &MatchedPath,
+    schema: Option<&crate::completion::SchemaCache>,
+) -> Vec<outcome::Diagnostic> {
+    use crate::dsl::grammar::IdentSource;
+    use crate::dsl::types::Type;
+    use outcome::{Diagnostic, MatchedKind, Severity};
+
+    let Some(schema) = schema else {
+        return Vec::new();
+    };
+    let Some(target) = path.items.iter().find_map(|it| match it.kind {
+        MatchedKind::Ident {
+            source: IdentSource::Tables,
+            role: "insert_target_table",
+        } => Some(it.text.as_str()),
+        _ => None,
+    }) else {
+        return Vec::new();
+    };
+    let Some(cols) = schema.columns_for_table(target) else {
+        return Vec::new();
+    };
+
+    let mut diagnostics = Vec::new();
+    for item in &path.items {
+        let MatchedKind::Ident {
+            source: IdentSource::Columns,
+            role: "insert_column",
+        } = item.kind
+        else {
+            continue;
+        };
+        if let Some(col) = cols
+            .iter()
+            .find(|c| c.name.eq_ignore_ascii_case(&item.text))
+            && matches!(col.user_type, Type::Serial | Type::ShortId)
+        {
+            diagnostics.push(Diagnostic {
+                severity: Severity::Warning,
+                span: item.span,
+                message: crate::friendly::translate(
+                    "diagnostic.auto_column_overridden",
+                    &[
+                        ("column", &item.text as &dyn std::fmt::Display),
+                        ("type", &col.user_type as &dyn std::fmt::Display),
+                    ],
+                ),
+            });
+        }
+    }
+    diagnostics
+}
+
 /// SQL-expression predicate-warning pass (ADR-0032 §11.6 — the
 /// Phase-1 carry-over gap closure).
 ///
@@ -2167,6 +2233,9 @@ fn walk_one_command<'a>(
         // operator slot is highlighted rather than the engine
         // wording shown at execution time.
         d.extend(compound_arity_diagnostics(&path));
+        // ADR-0033 §8.2 — WARNING when a SQL INSERT lists a
+        // serial/shortid (auto-generated) column explicitly.
+        d.extend(dml_auto_column_diagnostics(&path, ctx.schema));
         // ADR-0032 §10.3 / §11.2 — diagnostics emitted during
         // the walk by node handlers with direct context the
         // post-walk passes can't reconstruct (primarily the
@@ -3990,6 +4059,54 @@ mod tests {
         );
     }
 
+    #[test]
+    fn auto_column_overridden_fires_on_explicit_serial() {
+        // ADR-0033 §8.2: listing a serial column explicitly warns.
+        let schema = schema_with("t", &[("id", Type::Serial), ("name", Type::Text)]);
+        let diags = diag_keys("sqlinsert into t (id, name) values (5, 'x')", &schema);
+        assert!(
+            diags.iter().any(|d| d.contains("auto-generated")),
+            "explicit serial value should warn; got {diags:?}",
+        );
+    }
+
+    #[test]
+    fn auto_column_overridden_fires_on_explicit_shortid() {
+        let schema = schema_with("t", &[("id", Type::ShortId), ("name", Type::Text)]);
+        let diags = diag_keys("sqlinsert into t (id, name) values ('abc', 'x')", &schema);
+        assert!(
+            diags.iter().any(|d| d.contains("auto-generated")),
+            "explicit shortid value should warn; got {diags:?}",
+        );
+    }
+
+    #[test]
+    fn auto_column_overridden_silent_when_omitted() {
+        // Negative: omitting the auto-gen column does not warn.
+        let schema = schema_with("t", &[("id", Type::Serial), ("name", Type::Text)]);
+        let diags = diag_keys("sqlinsert into t (name) values ('x')", &schema);
+        assert!(
+            !diags.iter().any(|d| d.contains("auto-generated")),
+            "omitting the serial column must not warn; got {diags:?}",
+        );
+    }
+
+    #[test]
+    fn auto_column_overridden_conflict_target_not_flagged() {
+        // The ON CONFLICT (id) target names `id` but isn't an
+        // *inserted* value, so it must not trigger the warning;
+        // only the inserted `id` in the column list would.
+        let schema = schema_with("t", &[("id", Type::Serial), ("name", Type::Text)]);
+        let diags = diag_keys(
+            "sqlinsert into t (name) values ('x') on conflict (id) do nothing",
+            &schema,
+        );
+        assert!(
+            !diags.iter().any(|d| d.contains("auto-generated")),
+            "conflict-target serial column must not warn; got {diags:?}",
+        );
+    }
+
     #[test]
     fn upsert_excluded_resolves_in_do_update() {
         // ADR-0033 §9: inside a DO UPDATE action, `excluded.col`
diff --git a/src/friendly/keys.rs b/src/friendly/keys.rs
index 46f34a5..72203c9 100644
--- a/src/friendly/keys.rs
+++ b/src/friendly/keys.rs
@@ -39,6 +39,7 @@
 pub const KEYS_AND_PLACEHOLDERS: &[(&str, &[&str])] = &[
     // ---- Pre-submit diagnostics (ADR-0027) ----
     ("diagnostic.ambiguous_column", &["column", "qualifiers"]),
+    ("diagnostic.auto_column_overridden", &["column", "type"]),
     ("diagnostic.compound_arity_mismatch", &["op", "left_n", "right_n"]),
     ("diagnostic.cte_arity_mismatch", &["cte", "declared", "actual"]),
     ("diagnostic.duplicate_cte", &["name"]),
diff --git a/src/friendly/strings/en-US.yaml b/src/friendly/strings/en-US.yaml
index d6df488..6fb47bb 100644
--- a/src/friendly/strings/en-US.yaml
+++ b/src/friendly/strings/en-US.yaml
@@ -501,6 +501,8 @@ diagnostic:
   cte_arity_mismatch: "CTE `{cte}` declares {declared} columns but its body has {actual}"
   compound_arity_mismatch: "`{op}` requires both sides to have the same number of columns — left has {left_n}, right has {right_n}"
   duplicate_cte: "duplicate `WITH` table name: `{name}`"
+  # ADR-0033 §8 — Phase-3 DML diagnostic keys.
+  auto_column_overridden: "column `{column}` is auto-generated (`{type}`); providing an explicit value bypasses the auto-counter and may collide with later auto-generated values"
 
 # Engine-error translations: an engine-rejected SQL statement
 # reaches the friendly-error layer (ADR-0019) and these keys